Chicago skyline and shore of Lake Michigan

Chicago Vacation Packages

 
The third most populous city in the United States, Chicago sits perched on Lake Michigan, its skyscrapers glistening above the horizon. The iconic John Hancock Center, sky-high Willis Tower and Tribune Tower rise above the city's nearly three million residents.
 
  • Sheraton Grand Chicago Riverwalk
    Sheraton Grand Chicago Riverwalk
    Magnificent Mile, Chicago, IL Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    The Sheraton Grand Chicago Riverwalk is ideally located in the heart of downtown Chicago, overlooking the Chicago River.

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  • The Drake Hotel
    The Drake Hotel
    Magnificent Mile, Chicago, IL Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    This acclaimed hotel is an elegant symbol near Oak Street Beach at the onset of Chicago's Magnificent Mile, affording guests easy access to the city's most exclusive shopping, nightlife and dining.

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  • Palmer House a Hilton Hotel
    Palmer House a Hilton Hotel
    Magnificent Mile, Chicago, IL Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    This iconic downtown hotel offers guests the grandeur of tradition with an infusion of elegance.

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  • Hilton Chicago
    Hilton Chicago
    Magnificent Mile, Chicago, IL Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    Integrated into the Chicago skyline, this hotel near Grant Park rewards guests with the opportunity to immerse themselves within the city's architectural roots.

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  • DoubleTree by Hilton Chicago-Magnificent Mile
    DoubleTree by Hilton Chicago-Magnificent Mile
    Magnificent Mile, Chicago, IL Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This comfortable hotel is just two blocks from Michigan Avenue and the Magnificent Mile, offering easy access to Chicago’s most popular attractions.

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Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]